We bought our 04 in spring '11. got it for 26.5 plus tax, so like 28. Ours is the sammy duvall edition with wakeboard pro PP, No tower.
Your family sounds like ours, we sometimes ski right off the dock but other times will go across the lake a mile to ski the course. Sometimes that little cruise can be jarring, but it's only a mile (3 minutes) so it's not a huge deal. Now, pulling tubers on the 4th of July may warrant some dramamine....
I wouldn't trade the boat for any other! If it's too choppy we don't go out, which is fine because I use it mostly for course skiing.

Having new skins is a big value! We're getting the drive and observer seat done over the winter this year at a cost of about 500.